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Underwriting Analyst Captive

Starr Insurance · Chicago, IL · Full time

Posted Jul 13, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about your experience issuing quotes, binders or policies. What steps did you follow to avoid mistakes?

What they are checking: Real hands-on issuance experience and a checking routine, which the posting requires.

Tell me about a time you made an error at work. How did you find out and what did you do?

What they are checking: Honesty and ownership, since small issuance errors must be surfaced and fixed quickly.

How do you stay focused and accurate on repetitive administrative work?

What they are checking: Self-awareness about sustaining quality on detailed work over time.

What would you do

You need to collect renewal information, and the broker keeps missing deadlines. How do you keep the renewal on track?

What they are checking: Persistence and planning to protect renewal timelines without frustrating brokers.

Three underwriters hand you urgent work on the same morning. How do you decide what to do first?

What they are checking: Time management and communication, which the posting lists as innate skills it wants.

A renewal list shows an account expiring in two weeks with no submission started. What do you do?

What they are checking: Whether they use business logs proactively to prevent lapses.

About the work

What's your understanding of a captive insurance arrangement, and why would a company use one?

What they are checking: Basic grasp of the business this team supports, which helps them spot what matters in files.

Walk me through how you'd run account clearance on a new submission and what you'd do if it's already blocked.

What they are checking: Understanding of clearance and why it matters for broker relationships and avoiding duplicate quotes.

Tell me about a monthly report you built or maintained in Excel. How did you make sure the numbers were right?

What they are checking: Spreadsheet skill and data checking, since management reports drive decisions.

How do you organize underwriting files so someone else could pick one up and understand it?

What they are checking: Whether they keep files clean enough that audits and teammates can rely on them without asking.

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The full job description

As published by Starr Insurance.

Join Starr, a global leader in commercial insurance with over a century of expertise. We empower our employees to innovate, make impactful decisions, and build lasting client relationships worldwide. At Starr, you'll work in an entrepreneurial culture alongside accessible leaders, leveraging our financial strength and vast industry experience to deliver solutions for our clients, no matter how complex. Grow your career with a rapidly growing company that invests in its people and their ability to drive real progress. Duties and Responsibilities: • Maintain underwriting account clearance system • Issue quotes/binders/policies on behalf of underwriting staff • Create and maintain underwriting files • Collect renewal information and prepare renewal submissions for underwriters • Maintain business logs (renewal lists, etc.) as required • Prepare monthly reports as required Skills and Experience Required • Basic understanding of insurance products • Experience in the administrative process associated with quoting/binding accounts • Experience in the issuance of insurance policies • Ability to work alongside the underwriting staff in preparation of management reports • Demonstrate proficiency in computer applications: Excel, Word and PowerPoint • College diploma • Strong organizational skills • Innate time management capabilities • Ability to handle multiple tasks and prioritize • A “self-starter” and “problem solver” Starr is an equal opportunity employer, which means we'll consider all suitably qualified applicants regardless of gender identity or expression, ethnic origin, nationality, religion or beliefs, age, sexual orientation, disability status or any other protected characteristic. We recruit and develop our people based on merit and we're committed to creating an inclusive environment for all employees. We offer first class training and development opportunities to all employees. Our aim is to grow our own talent and bring out the best in people.

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